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Publications
Alkyl 2‐chloro‐2‐cyclopropylideneacetates 2 serve as universal starting materials for a new general synthesis of cyclopro‐pylglycines by a simple three‐ to four‐step methodology. 1,4‐Addition of nucleophiles, substitution with azide ion, and mild catalytic deprotection lead to a variety of salt‐free cyclopropyl‐substituted amino acids in good yields, including the natural products 2‐(1‐methylcyclopropyl)glycine (4 ) and cleonin (5 ).
Publications
Cyclopropylideneacetates (2a,b) undergo a formal [2 + 4] cycloaddition with (diphenylmethylene)amine (DPMA-H)(1) to yield dihydro-1-phenylisoquinoline-4-carboxylate (8a) and 1-phenylisoquinoline-4-carboxylate (7b); the Michael adduct of DPMA-H onto (2b), on the other hand, under basic conditions gives 1-phenyl-2-aza-azulene-3a-carboxylate (12) exclusively.
Publications
The syntheses and reactivities of some new cyclopropane containing C5-building blocks with composite functionalities are described. Recent applications of cyclopropylideneacetates in short syntheses of spirocyclopropane-annulated heterocycles and cyclopropane-containing biologically active compounds are demonstrated. Cyclopropylacetylenes are employed as cyclopentane annulation reagents and are particularly useful in the construction of terpenoid frameworks. 1. Introduction 2. The Initial Experiment: 1-Chloro-1-(trichlorovinyl)cyclopropanes from Olefins 3. Cyclopropylideneacetates 4. Cyclopropylacetylenes 5. Conclusion
Publications
(Diphenylmethylene)amine [benzophenone imine, DPMA-H] cleanly reacts with a variety of α,β-unsaturated esters, nitriles, ketones, and aldehydes 1a-q to give Michael type adducts 2a-q, generally, in respectable to excellent yields. Sterically congested and donor-substituted Michael acceptors do not react. The β-amino-substituted products can be further transformed in their protected form, or selectively deprotected under mild conditions, e.g. by catalytic hydrogenation.
Books and chapters
Cyclopropane amino acids have attracted the attention of synthetically and biologically oriented chemists throughout the last decade. Most efforts have been directed towards 1-aminocyclopropane carboxyclic acid (ACC), the natural precursor of the phytohormone ethylene,1 and its derivatives. Other natural cyclopropane amino acids as well as artificial ones were used as enzyme inhibitors for receptor and metabolism studies.2 We report here a new synthetic approach to a wide variety of cyclopropyl-substituted amino acids including the natural products cleonin (1) (1-hydroxycyclopropyl-glycin)3 and 1-methylcyclopropyl- glycin (2).4
This page was last modified on 27 Jan 2025 27 Jan 2025 .
